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AN EFFICIENT METHOD FOR ONE-POT SYNTHESIS OF 3-ALKOXY-SUBSTITUTED CHROMENO[4,3-b]PYRROL-4(1H)-ONE DERIVATIVES

Xiaofeng Yang, Lei Jing, Zhiwei Chen
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Abstract


A one-pot two-step reaction of 4-aminocoumarin with arylglyoxal monohydrates and p-toluenesulfonates has been developed, which offers 3-alkoxy-substituted chromeno[4,3-b]pyrrol-4(1H)-ones in moderate to good yields. At first, arylglyoxal monohydrates and 4-aminocoumarin were converted into 3-hydroxychromeno[4,3-b]pyrrol-4(1H)-one intermediates in AcOH under reflux. Then the title compounds in an in situ reaction of the intermediates with p-toluenesulfonates catalyzed by DBU in refluxing toluene were obtained.


Keywords


arylglyoxal monohydrates; pyrrolocoumarins; alkoxylation; heterocycle synthesis; one-pot synthesis

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